A sandal for a long day should stay put when I turn a corner, not merely look relaxed in a still photo. That is why the Chypre styles are worth comparing by strap and footbed. The red Chypre has Rouge H calfskin straps over a black rubber sole, while the blue and green pairs use suede goatskin and an adjustable H-cut upper.

The brown Chypre is the quieter option, and the metallic-gray version adds a glint without changing the sporty outline. White keeps the combination simple. The pink Chypre is glossy Mississippiensis alligator, a lot of color and texture in one small area. I would pair that one with a white shirt, straight jeans and very little else.

The Naxos sandal takes a different route, with rose-antique suede double straps and oversized buckles. I would wear it with a loose linen trouser, letting the buckle sit against a clean hem rather than compete with a busy print.

What I would skip: the pink Chypre when the rest of my outfit already has several strong colors. The sandal has enough presence on its own. At a fitting, adjust each fastening, then walk and pause with your weight on both feet. Check that the strap stays where you set it and that the rubber sole feels steady underfoot.

Heel height changes the whole rhythm of a sandal, so I would decide where the hem will land before choosing one. The black Milly 90 has a 3.5-inch heel and an adjustable ankle strap, a more deliberate choice for an evening outfit. The metallic Muse 40 sits lower, with its mini Kelly buckle and flared 1.6-inch heel.

For a softer line, the tan Milly 40 wraps the foot and ankle in calfskin straps above a low block heel. The black Noa 95 goes taller again, with a woven goatskin wedge and Chaine d’Ancre accents. I would wear the tan pair with a long skirt and save the black wedge for a hem that shows its shape.

The pre-owned Ilona 90 has a polished metal clasp, while the pre-owned Encens 50 has a broad H-front strap and block heel. The pre-owned Oasis in Etoupe is an H-cut style with a low heel, and the silver Oasis keeps that shape but makes it metallic.

For the pre-owned pairs, I would inspect the clasp, insole, sole and corners in the listing photos, then confirm the listed size and included accessories. Try the strap with your actual hem, and make sure the heel sits squarely when you stand. A lower pair should not get a pass on comfort just because it looks easy.

I would choose in this order: decide whether I need a flat sandal or a little lift, pick the hem I plan to wear, then settle on the color. The Santorini and Orans cover the simpler end; the Chypre makes sense when I want an adjustable strap and rubber sole.

After that, I would compare heel height in person and give any pre-owned pair a close look at the clasp, sole and insole. The small details change how a sandal feels once it is on, especially around the ankle.

The Oran began with a named place, and I like that it still gives me a clear starting point. The rest of the outfit can take it from there. If you want to keep browsing, I also put together A Flat Iron Has a Longer Past Than Your Morning Routine and Why I Went Back to Powder.